반응 #434823

반응 방정식

Sodium borohydride

2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

pyridine-3-carboxaldehyde

→

1-(3-Pyridyl)methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

용매

acetic acid methanol

반응 조건

후처리

1. 1
   온도at reflux for 18 h
2. 2
   workup.STIRRINGThe mixture was stirred for 2 h
3. 3
   기타evaporated in vacuo
4. 4
   기타The residue was partitioned between EtOAc and saturated sodium bicarbonate solution
5. 5
   세척The organic layer was washed with brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated in vacua
8. 8
   기타The residue was purified by flash chromatography on silica (eluant EtOAc)
9. 9
   기타to give a white solid

실험 절차

To solution of 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine from Example 15A (0.50 g, 3.38 mmol) in 1% acetic acid/methanol (25 ml), at room temperature, was added pyridine-3-carboxaldehyde (0.35 ml, 03.72 mmol). The mixture was stirred at reflux for 18 h and then allowed to cool to room temperature. Sodium borohydride (0.050 g, 0.80 mmol) was added. The mixture was stirred for 2 h and then evaporated in vacuo. The residue was partitioned between EtOAc and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacua. The residue was purified by flash chromatography on silica (eluant EtOAc) to give a white solid; yield 0.386 g (40%).

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